Method for combatting fish mycoses and one-celled ectoparasites

ABSTRACT

Fish mycoses and single-cell ectoparasites on fish are controlled using an active compound suitable for inhibiting the mitochondrial respiratory chain at the stage of the b/c 1  complex.

This application is a 371 of PCT/EP96/03354 filed Jul. 30, 1996.

The present invention relates to a method for controlling fish mycosesand single-cell ectoparasites on fish, which comprises using an activecompound suitable for inhibiting the mitochondrial respiratory chain atthe stage of the b/c₁ complex.

The invention additionally relates to compounds of the formula IA or IB##STR1## where . . . is a single or double bond and the index and thesubstituents have the following meanings:

R' is --C[CO₂ CH₃ ]═CHOCH₃, --C[CO₂ CH₃ ]═NOCH₃, --C[CONHCH₃ ]═NOCH₃,--C[CO₂ CH₃ ]═CHCH₃, --C[CO₂ CH₃ ]═CHCH₂ CH₃, --C[COCH₃ ]═NOCH₃,--C[COCH₂ CH₃ ]═NOCH₃, --N(OCH₃)--CO₂ CH₃, --N(CH₃)--CO₂ CH₃, --N(CH₂CH₃)--CO₂ CH₃,

R" is a C-organic radical,

a C-organic radical which is bonded directly or via an oxy, mercapto,amino or alkylamino group, or

together with a group X and the ring Q or T, to which they are bonded,are an unsubst. or subst. bicyclic, partially or completely unsaturatedsystem which, in addition to carbon ring members, can containheteroatoms from the group consisting of oxygen, sulfur and nitrogen,

R^(x) is --OC[CO₂ CH₃ ]═CHOCH₃, --OC[CO₂ CH₃ ]═CHCH₃, --OC[CO₂ CH₃]═CHCH₂ CH₃, --SC[CO₂ CH₃ ]═CHOCH₃, --SC[CO₂ CH₃ ]═CHCH₃, --SC[CO₂ CH₃]═CHCH₂ CH₃, --N(CH₃)C[CO₂ CH₃ ]═CHOCH₃, --N(CH₃)C[CO₂ CH₃ ]═NOCH₃,--CH₂ C[CO₂ CH₃ ]═CHOCH₃, --CH₂ C[CO₂ CH₃ ]═NOCH₃, --CH₂ C[CONHCH₃]═NOCH₃,

R^(y) is oxygen, sulfur, ═CH--or ═N--,

n is 0, 1, 2 or 3, where the radicals X can be different if n>1;

X is cyano, nitro, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄-alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or, in the case wheren>1, a C₃ -C₅ -alkylene, C₃ -C₅ -alkenylene, oxy-C₂ -C₄ -alkylene,oxy-C₁ -C₃ -alkylenoxy, oxy-C₂ -C₄ -alkenylene, oxy-C₂ -C₄ -alkenylenoxyor butadienediyl group bonded to two adjacent C atoms of the phenylring, where these chains in turn can carry one to three of the followingradicals: halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁-C₄ -haloalkoxy or C₁ -C₄ -alkylthio,

Y is ═C-- or --N--,

Q is phenyl, pyrrolyl, thienyl, furyl, pyrazolyl, imidazolyl, oxazolyl,isoxazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, 2-pyridonyl,pyrimidinyl or triazinyl,

T is phenyl, oxazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, pyridinyl,pyrimidinyl or triazinyl,

as an antimycotic, and compositions comprising these compounds suitablefor controlling fish mycoses and for controlling single-cellectoparasites and costiasis.

To date, only a few substances are known which are suitable forcontrolling fish mycoses and single-cell ectoparasites.

The preparation Malachite Green used mainly until now had to be takenoff the market because of its teratogenicity [cf. Meyer et al.,Transactions of the American Fisheries Society, 112, 818-824] andsuspicion of carcinogenicity. Other products (eg. formalin, potassiumpermanganate, sodium chloride) are only slightly active and in somecases have undesirably severe effects on the environment. Regarding theexisting possibilities of controlling fish parasites, see W.Schaperclaus, Fischkrankheiten (2nd part), 4th edition, Akademie-VerlagBerlin, 1979 and H.-H. Reichenbach-Klinke, Reichenbach-Kline's FishPathology, T.S.H. Publications Inc. Ltd., 1973.

Active compounds which inhibit the mitochondrial respiratory chain atthe stage of the b/c₁ complex are known from the literature asfungicides [cf. Dechema monographs Vol. 129, 27-38, VCHVerlagsgemeinschaft Weinheim 1993; Natural Product Reports 1993,565-574; Biochem. Soc. Trans. 22, 63S (1993)].

In particular, representatives of the active compounds of the formula I(or IA and IB) having fungicidal and in some cases also bioregulatoryaction are described in the following patents:

EP-A 178 826, EP-A 203 606, EP-A 203 608, EP-A 206 523,

EP-A 212 859, EP-A 226 917, EP-A 226 974, EP-A 242 070,

EP-A 242 081, EP-A 243 012, EP-A 243 014, EP-A 251 082,

EP-A 253 213, EP-A 254 426, EP-A 256 667, EP-A 260 794,

EP-A 260 832, EP-A 267 734, EP-A 273 572, EP-A 274 825,

EP-A 278 595, EP-A 280 185, EP-A 291 196, EP-A 299 694,

EP-A 307 101, EP-A 307 103, EP-A 310 954, EP-A 312 221,

EP-A 312 243, EP-A 329 011, EP-A 331 966, EP-A 335 519,

EP-A 336 211, EP-A 337 211, EP-A 341 845, EP-A 350 691,

EP-A 354 571, EP-A 363 818, EP-A 370 629, EP-A 373 775,

EP-A 374 811, EP-A 378 308, EP-A 378 755, EP-A 379 098,

EP-A 382 375, EP-A 383 117, EP-A 384 211, EP-A 385 224,

EP-A 385 357, EP-A 386 561, EP-A 386 681, EP-A 389 901,

EP-A 391 451, EP-A 393 428, EP-A 393 861, EP-A 398 692,

EP-A 400 417, EP-A 402 246, EP-A 405 782, EP-A 407 873,

EP-A 409 369, EP-A 414 153, EP-A 416 746, EP-A 420 091,

EP-A 422 597, EP-A 426 460, EP-A 429 968, EP-A 430 471,

EP-A 433 233, EP-A 433 899, EP-A 439 785, EP-A 459 285,

EP-A 460 575, EP-A 463 488, EP-A 463 513, EP-A 464 381,

EP-A 468 684, EP-A 468 695, EP-A 468 775, EP-A 471 261,

EP-A 472 224, EP-A 472 300, EP-A 474 042, EP-A 475 158,

EP-A 477 631, EP-A 480 795, EP-A 483 851, EP-A 483 985,

EP-A 487 409, EP-A 493 711, EP-A 498 188, EP-A 498 396,

EP-A 499 823, EP-A 503 436, EP-A 508 901, EP-A 509 857,

EP-A 513 580, EP-A 515 901, EP-A 517 301, EP-A 528 245,

EP-A 532 022, EP-A 532 126, EP-A 532 127, EP-A 535 980,

EP-A 538 097, EP-A 544 587, EP-A 546 387, EP-A 548 650,

EP-A 564 928, EP-A 566 455, EP-A 567 828, EP-A 571 326,

EP-A 579 071, EP-A 579 124, EP-A 579 908, EP-A 581 095,

EP-A 582 902, EP-A 582 925, EP-A 583 806, EP-A 584 625,

EP-A 585 751, EP-A 590 610, EP-A 596 254, WO-A 90/07,493,

WO-A 92/13,830, WO-A 92/18,487, WO-A 92/18,494, WO-A 92/21,653,

WO-A 93/07,116, WO-A 93/08,180, WO-A 93/08,183, WO-A 93/15,046,

WO-A 93/16,986, WO-A 94/00,436, WO-A 94/05,626, WO-A 94/08,948,

WO-A 94/08,968, WO-A 94/10,159, WO-A 94/11,334, JP-A 02/121,970,

JP-A 04/182,461, JP-A 05/201,946, JP-A 05/201,980,

JP-A 05/255,012, JP-A 05/294,948, JP-A 06/025,133,

JP-A 06/025,142, JP-A 06/056,756, FR-A 2 670 781, GB-A 2 210 041,

GB-A 2 218 702, GB-A 2 238 308, GB-A 2 249 092, GB-A 2 253 624,

GB-A 2 255 092, DE-A 39 05 911, EP-A 686 152, EP-A 691 950,

EP-A 627 411, EP-A 647 631, WO-A 95/21,156, WO-A 95/21,153,

WO-A 95/21,154, EP-A 673 923.

It is an object of the present invention to provide compositions forcontrolling fish mycoses and single-cell ectoparasites on fish whichhave good activity, are not concentrated in the fish to an undesiredextent and have no unacceptable effects on the biotic communities.

We have found that this object is achieved by the compositions definedat the outset.

Fundamentally all active compounds described in the patents mentioned atthe outset are suitable for the provision of the compositions accordingto the invention, where in particular the compounds mentioned in theexamples given there are to be taken into account. Of particularimportance in this case are compounds of the formulae IA and IB ##STR2##where R" is one of the following groups:

unsubst. or subst. aryloxy, unsubst. or subst. hetaryloxy, unsubst. orsubst. aryloxymethylene, unsubst. or subst. hetaryloxymethylene,unsubst. or subst. arylethenylene, unsubst. or subst. hetarylethenylene,or a group R.sup.α R.sup.β C═NOCH₂ -- or R.sup.γ ON═CR.sup.δ CR.sup.ε═NOCH₂ where the radicals R⁶⁰ , R.sup.β, R.sup.γ, R⁶⁷ and R⁶⁸ in generaland in particular have the meanings described in the following patents:

EP-A 370 629, EP-A 414 153, EP-A 426 460, EP-A 460 575,

EP-A 463 488, EP-A 472 300, EP-A 498 188, EP-A 498 396,

EP-A 515 901, EP-A 585 751, WO-A 90/07,493, WO-A 92/13,830,

WO-A 92/18,487, WO-A 92/18,494, WO-A 93/15,046, WO-A 93/16,986,

WO-A 94/08,948, WO-A 94/08,968, JP-A 05/201,946, JP-A 05/255,012,

JP-A 05/294,948, JP-A 06/025,133, JP-A 06/025,142,

WO-A 95/21,153 and WO-A 95/21,154.

Particularly preferred unsubst. or subst. aryloxy or unsubst. or subst.hetaryloxy radicals correspond in general and in particular to themeanings described in the following patents:

EP-A 178 826, EP-A 242 070, EP-A 242 081, EP-A 253 213,

EP-A 254 426, EP-A 256 667, EP-A 260 794, EP-A 280 185,

EP-A 307 103, EP-A 341 845, EP-A 382 375, EP-A 393 861,

EP-A 398 692, EP-A 405 782, EP-A 430 471, EP-A 468 684,

EP-A 468 695, EP-A 477 631, EP-A 483 985, EP-A 498 188,

EP-A 513 580, EP-A 515 901, WO-A 93/15,046, WO-A 94/10,159,

GB-A 2 253 624 and JP-A 04/182,461.

Particularly preferred unsubst. or subst. aryloxymethylene or unsubst.or subst. hetaryloxymethylene radicals correspond in general and inparticular to the meanings described in the following patents:

EP-A 178 826, EP-A 226 917, EP-A 253 213, EP-A 254 426, EP-A 278 595,EP-A 280 185, EP-A 299 694, EP-A 335 519, EP-A 350 691, EP-A 363 818,EP-A 373 775, EP-A 378 308, EP-A 385 224, EP-A 386 561, EP-A 398 692,EP-A 400 417, EP-A 407 873, EP-A 472 224, EP-A 477 631, EP-A 498 188,EP-A 498 396, EP-A 513 580, EP-A 515 901, EP-A 579 124, WO-A 93/08,180,WO-A 93/15,046, WO-A 94/00,436, JP-A 04/182,461, EP-A 686 152, EP-A 673923 and WO-A 95/29,896.

Particularly preferred unsubst. or subst. arylethenylene or unsubst. orsubst. hetarylethenylene radicals correspond in general and inparticular to the meanings described in the following patents:

EP-A 178 826, EP-A 203 606, EP-A 253 213, EP-A 254 426, EP-A 280 185,EP-A 378 755, EP-A 398 692, EP-A 402 246, EP-A 474 042, EP-A 475 158,EP-A 477 631, EP-A 487 409, EP-A 498 188, EP-A 498 396, EP-A 513 580,EP-A 515 901, EP-A 528 245, EP-A 544 587, WO-A 93/15,046, WO-A 94/11,334and FR-A 2 670 781 and EP-A 691 332.

Particularly preferred active compounds of the formula IA in which R' is--C[CO₂ CH₃ ]═CHOCH₃ correspond in general and in particular to thecompounds described in the following patents:

EP-A 178 826, EP-A 203 606, EP-A 226 917, EP-A 242 070, EP-A 242 081,EP-A 256 667, EP-A 260 794, EP-A 278 595, EP-A 299 694, EP-A 307 103,EP-A 335 519, EP-A 341 845, EP-A 350 691, EP-A 370 629, EP-A 373 775,EP-A 378 308, EP-A 378 755, EP-A 382 375, EP-A 385 224, EP-A 386 561,EP-A 414 153, EP-A 426 460, EP-A 430 471, EP-A 463 488, EP-A 468 695,EP-A 472 224, EP-A 474 042, EP-A 475 158, EP-A 483 985, EP-A 487 409,EP-A 515 901, EP-A 528 245, EP-A 544 587, WO-A 90/07,493, WO-A92/18,487, WO-A 92/18,494, WO-A 93/08,180, WO-A 93/16,986, WO-A94/00,436, WO-A 94/08,948, WO-A 94/08,968, WO-A 94/10,159, WO-A94/11,334, FR-A 2 670 781, JP-A 06/025,133, WO-A 95/21,153 and EP-A 673923.

Particularly preferred active compounds of the formula IA in which R' is--C[CO₂ CH₃ ]═NOCH₃ correspond in general and in particular to thecompounds described in the following patents:

EP-A 253 213, EP-A 254 426, EP-A 299 694, EP-A 363 818, EP-A 378 308,EP-A 385 224, EP-A 386 561, EP-A 400 417, EP-A 407 873, EP-A 460 575,EP-A 463 488, EP-A 468 684, EP-A 472 300, EP-A 515 901, WO-A 94/00,436,WO-A 94/08,948, WO-A 94/10,159, WO-A 94/11,334, JP-A 05/201,946, JP-A05/255,012, JP-A 05/294,948, WO-A 95/21,153 and EP-A 673 923.

Particularly preferred active compounds of the formula IA in which R' is--C[CONHCH₃ ]═NOCH₃ correspond in general and in particular to thecompounds described in the following patents:

EP-A 398 692, EP-A 463 488, EP-A 477 631, EP-A 515 901, EP-A 579 124,EP-A 585 751, WO-A 92/13,830, WO-A 93/08,180, WO-A 94/08,948, WO-A94/10,159, WO-A 94/11,334, GB-A 2 253 624, JP-A 04/182,461, JP-A05/201,946, JP-A 05/255,012, JP-A 05/294,948, EP-A 686 152, WO-A 21,154,EP-A 673 923 and EP-A 691 332.

Particularly preferred active compounds of the formula IA in which R' is--C[CO₂ CH₃ ]═CHCH₃ or --C[CO₂ CH₃ ]═CHCH₂ CH₃ correspond in general andin particular to the compounds described in the following patents:

EP-A 280 185, EP-A 463 488, EP-A 513 580, EP-A 515 901, WO-A 95/21,153,EP-A 673 923 and WO-A 95/29,896.

Particularly preferred active compounds of the formula IA in which R' is--C[COCH₃ ]═NOCH₃ or --C[COCH₂ CH₃ ]═NOCH₃ correspond in general and inparticular to the compounds described in EP-A 498 188.

Particularly preferred active compounds of the formula IA in which R' is--N(OCH₃)--CO₂ CH₃, --N(CH₃)--CO₂ CH₃ or --N(CH₂ CH₃)--CO₂ CH₃correspond in general and in particular to the compounds described inthe following patents: EP-A 498 396, WO-A 93/15,046, JP-A 06/025,142 andJP-A 06/056,756.

Particularly preferred active compounds of the formula IB in which R is--OC[CO₂ CH₃ ]═CHOCH₃, --OC[CO₂ CH₃ ]═CHCH₃, --OC[CO₂ CH₃ ]═CHCH₂ CH₃,--SC[CO₂ CH₃ ]═CHOCH₃, --SC[CO₂ CH₃ ]═CHCH₃, --SC[CO₂ CH₃ ]═CHCH₂ CH₃,--N(CH₃)C[CO₂ CH₃ ]═CHOCH₃, --N(CH₃)C[CO₂ CH₃ ]═NOCH₃, --CH₂ C[CO₂ CH₃]═CHOCH₃, --CH₂ C[CO₂ CH₃ ]═NOCH₃ or --CH₂ C[CONHCH₃ ]═NOCH₃ correspondin general and in particular to the compounds described in the followingpatents:

EP-A 212 859, EP-A 331 966, EP-A 383 117, EP-A 384 211, EP-A 389 901,EP-A 409 369, EP-A 464 381, EP-A 471 261, EP-A 503 436, EP-A 546 387,EP-A 548 650, EP-A 579 908 and EP-A 584 625.

Examples of particularly suitable active compounds IA and IB arecompiled in the following tables.

                  TABLE I.1A                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(CO.sub.2 CH.sub.3)═CHOCH.sub.3, n has the value 0, R" is unsubst.     or subst.                                                                     (het)aryloxymethylene, where the unsubst. or subst. (het)aryl                 group has the following meanings                                              No.      Unsubst. or subst. (het)aryl                                                                      Reference                                        ______________________________________                                        I.1A-1   2-CH.sub.3 --C.sub.6 H.sub.4                                                                      EP-A 226 917                                     I.1A-2   2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                                            EP-A 226 917                                     I.1A-3   2-CH.sub.3, 4-C[CH.sub.3 ]═NOCH.sub.3 --C.sub.6 H.sub.3                                       EP-A 386 561                                     I.1A-4   2-CH.sub.2 CH.sub.2 CH.sub.3, 6-CF.sub.3 -pyrimidin-4-yl                                          EP-A 407 873                                     ______________________________________                                    

                  TABLE I.1B                                                      ______________________________________                                        Compounds of the formula IA, in which R' is --C(CO.sub.2 CH.sub.3)═CHO    CH.sub.3,                                                                     Q is phenyl, n has the value 0, R" is unsubst. or subst.                      (het)aryloxy, where the unsubst. or subst. (het)aryl group has                the following meanings                                                        No.      Unsubst. or subst. (het)aryl                                                                      Reference                                        ______________________________________                                        I.1B-1   C.sub.6 H.sub.5     EP-A 178 826                                     I.1B-2   6-[2-CN--C.sub.6 H.sub.4 --O]-pyrimidin-4-yl                                                      EP-A 382 375                                     ______________________________________                                    

                  TABLE I.1C                                                      ______________________________________                                        Compounds of the formula IA, in which R' is --C(CO.sub.2 CH.sub.3)═CHO    CH.sub.3,                                                                     Q is phenyl, n has the value 0, R" is unsubst. or subst.                      (het)arylethenylene, where die unsubst. or subst. (het)aryl group             has the following meanings                                                    No.    Unsubst. or subst. (het)aryl                                                                        Reference                                        ______________________________________                                        I.1C-1 1-(2,4-Cl.sub.2 --C.sub.6 H.sub.3), 5-CF.sub.3 -pyrazol-4-yl                                        EP-A 528 245                                     I.1C-2 1-(4-Cl--C.sub.6 H.sub.4)-pyrazol-4-yl                                                              EP-A 378 755                                     I.1C-3 3-CF.sub.3 --C.sub.6 H.sub.4                                                                        EP-A 203 606                                     I.1C-4 3-Cl--C.sub.6 H.sub.4 EP-A 203 606                                     I.1C-5 4-C.sub.6 H.sub.5 --C.sub.6 H.sub.4                                                                 EP-A 203 606                                     ______________________________________                                    

                  TABLE I.1D                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(CO.sub.2 CH.sub.3)═CHOCH.sub.3, n has the value 0, R" is              CH.sub.2 ON═CR.sup.α R.sup.β, where R.sup.α  and         R.sup.β  have the following meanings                                     No.    R.sup.α                                                                         R.sup.β     Reference                                     ______________________________________                                        I.1D-1 CH.sub.3                                                                              4-Cl--C.sub.6 H.sub.4                                                                          EP-A 370 629                                  I.1D-2 CH.sub.3                                                                              3-CF.sub.3 --C.sub.6 H.sub.4                                                                   EP-A 370 629                                  I.1D-3 CH.sub.3                                                                              4-OCH.sub.2 CH.sub.3 -pyrimidin-2-yl                                                           WO-A 92/18,487                                ______________________________________                                    

                  TABLE I.1E                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(CO.sub.2 CH.sub.3)═CHOCH.sub.3, n has the value 0, R" is              CH.sub.2 ON═CR.sup.γ R.sup.δ ═NOR.sup.ε,          where R.sup.γ, R.sup.δ  and                                       R.sup.ε  have the following meanings                                  No.    R.sup.γ                                                                         R.sup.δ                                                                            R.sup.ε                                                                       Reference                                   ______________________________________                                        I.1E-1 CH.sub.3                                                                              CH.sub.3   CH.sub.3                                                                              WO-A 95/21,153                              I.1E-2 CH.sub.3                                                                              CH.sub.3   CH.sub.2 CH.sub.3                                                                     WO-A 95/21,153                              I.1E-3 CH.sub.3                                                                              C.sub.6 H.sub.5                                                                          CH.sub.3                                                                              WO-A 95/21,153                              I.1E-4 CH.sub.3                                                                              C.sub.6 H.sub.5                                                                          CH.sub.2 CH.sub.3                                                                     WO-A 95/21,153                              I.1E-5 CH.sub.3                                                                              4-Cl--C.sub.6 H.sub.4                                                                    CH.sub.3                                                                              WO-A 95/21,153                              I.1E-6 CH.sub.3                                                                              4-Cl--C.sub.6 H.sub.4                                                                    CH.sub.2 CH.sub.3                                                                     WO-A 95/21,153                              ______________________________________                                    

                  TABLE I.2A                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(CO.sub.2 CH.sub.3)═NOCH.sub.3, n has the value 0, R" is               unsubst. or subst. (het)aryloxymethylene, where the unsubst. or               subst. (het)aryl group has the following meanings                             No.      Unsubst. or subst. (het)aryl                                                                      Reference                                        ______________________________________                                        I.2A-1   2-CH.sub.3 --C.sub.6 H.sub.4                                                                      EP-A 253 213                                     I.2A-2   2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                                            EP-A 400 417                                     I.2A-3   2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                                            EP-A 400 417                                     I.2A-4   2,3,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                                                          EP-A 400 417                                     I.2A-5   2-Cl, 5-CH.sub.3 --C.sub.6 H.sub.3                                                                EP-A 400 417                                     I.2A-6   2-CH.sub.3, 4-C[CH.sub.3 ]═NOCH.sub.3 --C.sub.6 H.sub.3                                       EP-A 386 561                                     ______________________________________                                    

                  TABLE I.2B                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(CO.sub.2 CH.sub.3)═NOCH.sub.3, n has the value 0, R" is               unsubst. or subst. (het)aryloxy, where the unsubst. or                        subst. (het)aryl group has the following meanings                             No.      Unsubst. or subst. (het)aryl                                                                      Reference                                        ______________________________________                                        I.2B-1   C.sub.6 H.sub.5     EP-A 253 213                                     I.2B-2   6-[2-CN--C.sub.6 H.sub.4 --O]-pyrimidin-4-yl                                                      EP-A 468 684                                     ______________________________________                                    

                  TABLE I.2C                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(CO.sub.2 CH.sub.3)═NOCH.sub.3, n has the value 0, R" is               CH.sub.2 ON═CR.sup.α R.sup.β, where R.sup.α  and         R.sup.β  have the following meanings                                     No.     R.sup.α                                                                          R.sup.β    Reference                                    ______________________________________                                        I.2C-1  CH.sub.3 4-Cl--C.sub.6 H.sub.4                                                                         EP-A 463 488                                 I.2C-2  CH.sub.3 3-Cl--C.sub.6 H.sub.4                                                                         EP-A 463 488                                 I.2C-3  CH.sub.3 4-CF.sub.3 --C.sub.6 H.sub.4                                                                  EP-A 463 488                                 I.2C-4  CH.sub.3 3-CF.sub.3 --C.sub.6 H.sub.4                                                                  EP-A 463 488                                 I.2C-5  CH.sub.3 4-CH.sub.3 --C.sub.6 H.sub.4                                                                  EP-A 463 488                                 I.2C-6  CH.sub.3 4-OCH.sub.2 CH.sub.3 -pyrimidin-2-yl                                                          EP-A 472 300                                 I.2C-7  CH.sub.3 3,5-Cl.sub.2 --C.sub.6 H.sub.3                                                                EP-A 463 488                                 ______________________________________                                    

                  TABLE I.2D                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(CO.sub.2 CH.sub.3)═NOCH.sub.3, n has the value 0, R" is               CH.sub.2 ON═CR.sup.γ CR.sup.δ ═NOR.sup.ε,         where                                                                         R.sup.γ, R.sup.δ  and R.sup.ε  have the following         meanings                                                                      No.    R.sup.γ                                                                         R.sup.δ                                                                            R.sup.ε                                                                       Reference                                   ______________________________________                                        I.2D-1 CH.sub.3                                                                              CH.sub.3   CH.sub.3                                                                              WO-A 95/21,153                              I.2D-2 CH.sub.3                                                                              CH.sub.3   CH.sub.2 CH.sub.3                                                                     WO-A 95/21,153                              I.2D-3 CH.sub.3                                                                              C.sub.6 H.sub.5                                                                          CH.sub.3                                                                              WO-A 95/21,153                              I.2D-4 CH.sub.3                                                                              C.sub.6 H.sub.5                                                                          CH.sub.2 CH.sub.3                                                                     WO-A 95/21,153                              I.2D-5 CH.sub.3                                                                              4-Cl--C.sub.6 H.sub.4                                                                    CH.sub.3                                                                              WO-A 95/21,153                              I.2D-6 CH.sub.3                                                                              4-Cl--C.sub.6 H.sub.4                                                                    CH.sub.2 CH.sub.3                                                                     WO-A 95/21,153                              ______________________________________                                    

                  TABLE I.3A                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(CONHCH.sub.3)═NOCH.sub.3, n has the value 0, R" is unsubst. or        subst.                                                                        (het)aryloxymethylene, where the unsubst. or subst. (het)aryl                 group has the following meanings                                              No.      Unsubst. or subst. (het)aryl                                                                      Reference                                        ______________________________________                                        I.3A-1   2-CH.sub.3 --C.sub.6 H.sub.4                                                                      EP-A 477 631                                     I.3A-2   2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                                            EP-A 477 631                                     I.3A-3   2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                                            EP-A 477 631                                     I.3A-4   2,3,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                                                          EP-A 477 631                                     I.3A-5   2-CH.sub.3, 4-C[CH.sub.3 ]═NOCH.sub.3 --C.sub.6 H.sub.3                                       EP-A 579 124                                     I.3A-6   1-[4-Cl--C.sub.6 H.sub.4 ]-pyrazol-3-yl                                                           EP-A 686 152                                     I.3A-7   1-[2,4-Cl.sub.2 --C.sub.6 H.sub.3 ]-pyrazol-3-yl                                                  EP-A 686 152                                     ______________________________________                                    

                  TABLE I.3B                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(CONHCH.sub.3)═NOCH.sub.3, n has the value 0, R" is unsubst. or        subst.                                                                        (het)aryloxy, where the unsubst. or subst. (het)aryl group has                the following meanings                                                        No.    Unsubst. or subst. (het)aryl                                                                       Reference                                         ______________________________________                                        I.3B-1 C.sub.6 H.sub.5      EP-A 398 692                                      I.3B-2 6-[2-CN--C.sub.6 H.sub.4 --O]-pyrimidin-4-yl                                                       GB-A 2 253 624                                    ______________________________________                                    

                  TABLE I.3C                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(CONHCH.sub.3)═NOCH.sub.3, n has the value 0, R" is unsubst. or        subst.                                                                        (het)arylethenylene, where the unsubst. or subst. (het)aryl group             has the following meanings                                                    No.       Unsubst. or subst. (het)aryl                                                                  Reference                                           ______________________________________                                        I.3C-1    1-[2,4-Cl.sub.2 --C.sub.6 H.sub.3 ],                                                          EP-A 691 332                                                  5-CF.sub.3 -pyrazol-4-yl                                            ______________________________________                                    

                  TABLE I.3D                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(CONHCH.sub.3)═NOCH.sub.3, n has the value 0, R" is CH.sub.2           ON═CR.sup.α R.sup.β,                                           where R.sup.α  and R.sup.β  have the following meanings            No.    R.sup.α                                                                         R.sup.β     Reference                                     ______________________________________                                        I.3D-1 CH.sub.3                                                                              4-Cl--C.sub.6 H.sub.4                                                                          EP-A 463 488                                  I.3D-2 CH.sub.3                                                                              3-Cl--C.sub.6 H.sub.4                                                                          EP-A 463 488                                  I.3D-3 CH.sub.3                                                                              4-CF.sub.3 --C.sub.6 H.sub.4                                                                   EP-A 585 751                                  I.3D-4 CH.sub.3                                                                              3-CF.sub.3 --C.sub.6 H.sub.4                                                                   EP-A 585 751                                  I.3D-5 CH.sub.3                                                                              4-CH.sub.3 --C.sub.6 H.sub.4                                                                   EP-A 463 488                                  I.3D-6 CH.sub.3                                                                              3,5-Cl.sub.2 --C.sub.6 H.sub.3                                                                 EP-A 463 488                                  I.3D-7 CH.sub.3                                                                              2-OCH.sub.2 CH.sub.3 -pyrimidin-2-yl                                                           WO-A 92/13,830                                ______________________________________                                    

                  TABLE I.3E                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(CONHCH.sub.3)═NOCH.sub.3, n has the value 0, R" is                    CH.sub.2 ON═CR.sup.γ CR.sup.δ ═NOR.sup.ε,         where R.sup.γ, R.sup.δ  and R.sup.ε                       have the following meanings                                                   No.    R.sup.γ                                                                         R.sup.δ                                                                            R.sup.ε                                                                       Reference                                   ______________________________________                                        I.3E-1 CH.sub.3                                                                              CH.sub.3   CH.sub.3                                                                              WO-A 95/21,154                              I.3E-2 CH.sub.3                                                                              CH.sub.3   CH.sub.2 CH.sub.3                                                                     WO-A 95/21,154                              I.3E-3 CH.sub.3                                                                              C.sub.6 H.sub.5                                                                          CH.sub.3                                                                              WO-A 95/21,154                              I.3E-4 CH.sub.3                                                                              C.sub.6 H.sub.5                                                                          CH.sub.2 CH.sub.3                                                                     WO-A 95/21,154                              I.3E-5 CH.sub.3                                                                              4-Cl--C.sub.6 H.sub.4                                                                    CH.sub.3                                                                              WO-A 95/21,154                              I.3E-6 CH.sub.3                                                                              4-Cl--C.sub.6 H.sub.4                                                                    CH.sub.2 CH.sub.3                                                                     WO-A 95/21,154                              ______________________________________                                    

                  TABLE I.4A                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(CO.sub.2 CH.sub.3)═CHCH.sub.3, n has the value 0, R" is unsubst.      or subst.                                                                     (het)aryloxymethylene, where the unsubst. or subst. (het)aryl                 group has the following meanings                                              No.    Unsubst. or subst. (het)aryl                                                                       Reference                                         ______________________________________                                        I.4A-1 2-CH.sub.3 --C.sub.6 H.sub.4                                                                       EP-A 280 185                                      I.4A-2 2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                                             EP-A 513 580                                      I.4A-3 2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                                             EP-A 513 580                                      I.4A-4 2,3,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                                                           EP-A 513 580                                      I.4A-5 2-Cl, 5-CH.sub.3 --C.sub.6 H.sub.3                                                                 EP-A 513 580                                      I.4A-6 2-CH.sub.3, 4-C[CH.sub.3 ]═NOCH.sub.3 --C.sub.6 H.sub.3                                        EP-A 513 580                                      I.4A-7 1-[4-Cl--C.sub.6 H.sub.4 ]-pyrazol-3-yl                                                            WO-A 95/29,896                                    ______________________________________                                    

                  TABLE I.4B                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(CO.sub.2 CH.sub.3)═CHCH.sub.3, n has the value 0, R" is unsubst.      or subst.                                                                     (het)aryloxy, where the unsubst. or subst. (het)aryl group has                the following meanings                                                        No.       Unsubst. or subst. (het)aryl                                                                  Reference                                           ______________________________________                                        I.4B-1    C.sub.6 H.sub.5 EP-A 513 580                                        ______________________________________                                    

                  TABLE I.4C                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(CO.sub.2 CH.sub.3)═CHCH.sub.3, n has the value 0, R" is               CH.sub.2 ON═CR.sup.γ CR.sup.δ ═NOR.sup.ε,         where R.sup.γ, R.sup.δ  and R.sup.ε                       have the following meanings                                                   No.    R.sup.γ                                                                         R.sup.δ                                                                            R.sup.ε                                                                       Reference                                   ______________________________________                                        I.4C-1 CH.sub.3                                                                              CH.sub.3   CH.sub.3                                                                              WO-A 95/21,153                              I.4C-2 CH.sub.3                                                                              CH.sub.3   CH.sub.2 CH.sub.3                                                                     WO-A 95/21,153                              I.4C-3 CH.sub.3                                                                              C.sub.6 H.sub.5                                                                          CH.sub.3                                                                              WO-A 95/21,153                              I.4C-4 CH.sub.3                                                                              C.sub.6 H.sub.5                                                                          CH.sub.2 CH.sub.3                                                                     WO-A 95/21,153                              I.4C-5 CH.sub.3                                                                              4-Cl--C.sub.6 H.sub.4                                                                    CH.sub.3                                                                              WO-A 95/21,153                              I.4C-6 CH.sub.3                                                                              4-Cl--C.sub.6 H.sub.4                                                                    CH.sub.2 CH.sub.3                                                                     WO-A 95/21,153                              ______________________________________                                    

                  TABLE I.5A                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(CO.sub.2 CH.sub.3)═CHCH.sub.2 CH.sub.3, n has the value 0, R" is      unsubst. or subst.                                                            (het)aryloxymethylene, where the unsubst. or subst. (het)aryl                 group has the following meanings                                              No.      Unsubst. or subst. (het)aryl                                                                      Reference                                        ______________________________________                                        I.5A-1   2-CH.sub.3 --C.sub.6 H.sub.4                                                                      EP-A 513 580                                     I.5A-2   2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                                            EP-A 513 580                                     I.5A-3   2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                                            EP-A 513 580                                     I.5A-4   2,3,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                                                          EP-A 513 580                                     I.5A-5   2-Cl, 5-CH.sub.3 --C.sub.6 H.sub.3                                                                EP-A 513 580                                     I.5A-6   2-CH.sub.3, 4-C[CH.sub.3 ]═NOCH.sub.3 --C.sub.6 H.sub.3                                       EP-A 513 580                                     ______________________________________                                    

                  TABLE I.5B                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(CO.sub.2 CH.sub.3)═CHCH.sub.2 CH.sub.3, n has the value 0, R" is      unsubst. or subst.                                                            (het)aryloxy, where the unsubst. or subst. (het)aryl group has                the following meanings                                                        No.       Unsubst. or subst. (het)aryl                                                                  Reference                                           ______________________________________                                        I.5B-1    C.sub.6 H.sub.5 EP-A 513 580                                        ______________________________________                                    

                  TABLE I.5C                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R'                         is --C(CO.sub.2 CH.sub.3)═CHCH.sub.2 CH.sub.3, n has the value 0, R"      is                                                                            CH.sub.2 ON═CR.sup.γ CR.sup.δ ═NOR.sup.ε,         where R.sup.γ, R.sup.δ  and R.sup.ε                       have the following meanings                                                   No.    R.sup.γ                                                                         R.sup.δ                                                                            R.sup.ε                                                                       Reference                                   ______________________________________                                        I.5C-1 CH.sub.3                                                                              CH.sub.3   CH.sub.3                                                                              WO-A 95/21,153                              I.5C-2 CH.sub.3                                                                              CH.sub.3   CH.sub.2 CH.sub.3                                                                     WO-A 95/21,153                              I.5C-3 CH.sub.3                                                                              C.sub.6 H.sub.5                                                                          CH.sub.3                                                                              WO-A 95/21,153                              I.5C-4 CH.sub.3                                                                              C.sub.6 H.sub.5                                                                          CH.sub.2 CH.sub.3                                                                     WO-A 95/21,153                              I.5C-5 CH.sub.3                                                                              4-Cl--C.sub.6 H.sub.4                                                                    CH.sub.3                                                                              WO-A 95/21,153                              I.5C-6 CH.sub.3                                                                              4-Cl--C.sub.6 H.sub.4                                                                    CH.sub.2 CH.sub.3                                                                     WO-A 95/21,153                              ______________________________________                                    

                  TABLE I.6A                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(COCH.sub.3)═NOCH.sub.3, n has the value 0, R" is unsubst. or          subst.                                                                        (het)aryloxymethylene, where the unsubst. or subst. (het)aryl                 group has the following meanings                                              No.      Unsubst. or subst. (het)aryl                                                                      Reference                                        ______________________________________                                        I.6A-1   2-CH.sub.3 --C.sub.6 H.sub.4                                                                      EP-A 498 188                                     I.6A-2   2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                                            EP-A 498 188                                     I.6A-3   2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                                            EP-A 498 188                                     I.6A-4   2,3,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                                                          EP-A 498 188                                     I.6A-5   2-CH.sub.3, 4-C[CH.sub.3 ]═NOCH.sub.3 --C.sub.6 H.sub.3                                       EP-A 498 188                                     ______________________________________                                    

                  TABLE I.6B                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(COCH.sub.3)═NOCH.sub.3, n has the value 0, R" is unsubst. or          subst.                                                                        (het)aryloxy, where the unsubst. or subst. (het)aryl group has                the following meanings                                                        No.      Unsubst. or subst. (het)aryl                                                                      Reference                                        ______________________________________                                        I.6B-1   C.sub.6 H.sub.5     EP-A 498 188                                     I.6B-2   6-[2-CN--C.sub.6 H.sub.4 --O]-pyrimidin-4-yl                                                      EP-A 498 188                                     ______________________________________                                    

                  TABLE I.7A                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(COCH.sub.2 CH.sub.3)═NOCH.sub.3, n has the value 0, R" is             unsubst. or subst.                                                            (het)aryloxymethylene, where the unsubst. or subst. (het)aryl                 group has the following meanings                                              No.      Unsubst. or subst. (het)aryl                                                                      Reference                                        ______________________________________                                        I.7A-1   2-CH.sub.3 --C.sub.6 H.sub.4                                                                      EP-A 498 188                                     I.7A-2   2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                                            EP-A 498 188                                     I.7A-3   2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                                            EP-A 498 188                                     I.7A-4   2,3,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                                                          EP-A 498 188                                     I.7A-5   2-CH.sub.3, 4-C[CH.sub.3 ]═NOCH.sub.3 --C.sub.6 H.sub.3                                       EP-A 498 188                                     ______________________________________                                    

                  TABLE I.7B                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --C(COCH.sub.2 CH.sub.3)═NOCH.sub.3, n has the value 0, R" is             unsubst. or subst.                                                            (het)aryloxy, where the unsubst. or subst. (het)aryl group has                the following meanings                                                        No.      Unsubst. or subst. (het)aryl                                                                      Reference                                        ______________________________________                                        I.7B-1   C.sub.6 H.sub.5     EP-A 498 188                                     I.7B-2   6-[2-CN--C.sub.6 H.sub.4 --O]-pyrimidin-4-yl                                                      EP-A 498 188                                     ______________________________________                                    

                  TABLE I.8A                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --N(OCH.sub.3)--CO.sub.2 CH.sub.3, n has the value 0, R" is unsubst. or       subst.                                                                        (het)aryloxymethylene, where the unsubst. or subst. (het)aryl                 group has the following meanings                                              No.   Unsubst. or subst. (het)aryl                                                                         Reference                                        ______________________________________                                        I.8A-1                                                                              2-CH.sub.3 --C.sub.6 H.sub.4                                                                         WO-A 93/15,046                                   I.8A-2                                                                              2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                                               WO-A 93/15,046                                   I.8A-3                                                                              2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                                               WO-A 93/15,046                                   I.8A-4                                                                              2,3,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                                                             WO-A 93/15,046                                   I.8A-5                                                                              2-Cl, 5-CH.sub.3 --C.sub.6 H.sub.3                                                                   WO-A 93/15,046                                   I.8A-6                                                                              2-CH.sub.3, 4-C[CH.sub.3 ]═NOCH.sub.3 --C.sub.6 H.sub.3                                          WO-A 93/15,046                                   I.8A-7                                                                              2-CH.sub.3, 4-C[CH.sub.3 ]═NOCH.sub.2 CH.sub.3 --C.sub.6                  H.sub.3                WO-A 93/15,046                                   I.8A-8                                                                              2-CH.sub.3, 4-C[CH.sub.2 CH.sub.3 ]═NOCH.sub.3 --C.sub.6                  H.sub.3                WO-A 93/15,046                                   I.8A-9                                                                              2-CH.sub.3, 4-C[CH.sub.2 CH.sub.3 ]═NOCH.sub.2 CH.sub.3                   --C.sub.6 H.sub.3      WO-A 93/15,046                                   I.8A-10                                                                             1-[4-Cl--C.sub.6 H.sub.4 ]-pyrazol-3-yl                                                              WO-A 96/01,256                                   ______________________________________                                    

                  TABLE I.8B                                                      ______________________________________                                        Compounds of the formula IA, in which Q is phenyl, R' is                      --N(OCH.sub.3)--CO.sub.2 CH.sub.3, n has the value 0, R" is CH.sub.2          ON═CR.sup.α R.sup.β,                                           where R.sup.α  and R.sup.β  have the following meanings            No.     R.sup.α                                                                            R.sup.β                                                                             Reference                                       ______________________________________                                        I.8B-1  CH.sub.3   3,5-Cl.sub.2 --C.sub.6 H.sub.3                                                           WO-A 93/15,046                                  ______________________________________                                    

It is to be assumed according to previous knowledge that the effectaccording to the invention of the control of fish mycoses andsingle-cell ectoparasites in fish can be employed in all fishpopulations, in particular in breeding ponds, breeding tanks andaquaria, natural game fish waters and marine fish farms.

The compositions according to the invention are particularly suitablefor treating Cyprinidae, Percidae and Salmonidae and other breeding andornamental fish.

In particular, the compositions according to the invention are suitablefor controlling branchiomycosis and saprolegniasis in fish, and theiregg, larval and juvenile stages.

The compositions according to the invention are furthermore suitable forcontrolling, in particular, single-cell ectoparasites on fish, thefollowing being mentioned by way of example: Ichthyophthirius sp.,Chilodonella sp., Trichodina sp. and Ichthyobodo.

The symptoms of costiasis caused by such parasites can be controlled bythe active compounds of the formulae IA, IB and IC according to theinvention.

The application rates of compounds I.A and I.B are, depending on thetype and development stage of the fish, from 0.1 μg/l to 5 mg/l,preferably 0.3 μg/l to 3 mg/l, in particular 1 μg/l to 1 mg/l,particularly preferably 5 μg/l to 500 μg/l. Higher concentrations aregenerally not necessary, but can be useful in the treatment of egg,larval and juvenile stages, depending on the type of compound,particularly in artificial systems (eg. breeding tanks or aquaria).

The compounds I.A and I.B can be used directly or mixed with customaryinert carriers before use. Those substances are fundamentally suitableas inert carriers which facilitate or guarantee a homogeneousdistribution of the active compound in the water.

The compositions are prepared in a known manner, eg. by extending theactive compound with solvents and/or carriers, if desired usingemulsifiers and dispersants, where if water is used as a diluent otherorganic solvents can also be used as auxiliary solvents.

Suitable auxiliaries for this purpose are essentially:

solvents such as aromatics (eg. xylene), chlorinated aromatics (eg.chlorobenzenes), paraffins (eg. petroleum fractions), alcohols (eg.methanol, butanol), ketones (eg. cyclohexanone), amines (eg.ethanolamine, dimethylformamide) and water;

carriers such as ground natural minerals (eg. kaolins, argilaceousearths, talc, chalk) and ground synthetic minerals (eg. highly dispersesilica, silicates);

emulsifiers such as nonionic and anionic emulsifiers (eg.polyoxyethylene fatty alcohol ethers, alkylsulfonates andarylsulfonates) and

dispersants such as lignin sulfite waste liquors and methylcellulose.

Suitable surface-active substances are the alkali metal, alkaline earthmetal or ammonium salts of aromatic sulfonic acids, eg. lignosulfonic,phenolsulfonic, naphthalenesulfonic and dibutylnaphthalenesulfonic acid,as well as of fatty acids, alkyl- and alkylarylsulfonates, alkyl, laurylether and fatty alcohol sulfates, and also salts of sulfated hexa-,hepta- and octadecanols, as well as of fatty alcohol glycol ethers,condensation products of sulfonated naphthalene and its derivatives withformaldehyde, condensation products of naphthalene or of thenaphthalenesulfonic acids with phenol and formaldehyde, polyoxyethyleneoctylphenyl ether, ethoxylated isooctyl-, octyl- or nonylphenol,alkylphenyl or tributylphenyl polyglycol ether, alkylaryl polyetheralcohols, isotridecyl alcohol, fatty alcohol-ethylene oxide condensates,ethoxylated castor oil, polyoxyethylene or polyoxypropylene alkylethers, lauryl alcohol polyglycol ether acetate, sorbitol esters,lignin-sulfite waste liquors or methylcellulose.

Aqueous application forms can be prepared from emulsion concentrates,dispersions, pastes, wettable powders or water-dispersible granules byaddition of water. To prepare emulsions, pastes or oil dispersions, thesubstances can be homogenized as such, or dissolved in an oil orsolvent, by means of wetting agents, adherents, dispersants oremulsifiers. However, concentrates consisting of active substance,wetting agent, adherent, dispersant or emulsifier and possibly solventor oil which are suitable for dilution with water can also be prepared.

Powder, broadcasting and dusting compositions can be prepared by mixingor joint grinding of the active substances with a solid carrier.

Granules, eg. coated, impregnated and homogeneous granules can beprepared by binding the active compounds to solid carriers.

Solid carriers are mineral earths such as silicic acids, silica gels,silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay,dolomite, diatomaceous earth, calcium sulfate and magnesium sulfate,magnesium oxide, ground synthetic materials, fertilizers, such asammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, andvegetable products, such as grain meal, tree bark, wood and nutshellmeal, cellulose powder or other solid carriers. The active compoundconcentrations in the ready-to-use preparations can be varied withinrelatively wide ranges.

Very generally, the compositions contain from 0.0001 to 95% by weight ofactive compound.

Formulations containing more than 95% by weight of active compound canbe applied with great success in the ultra-low volume process (ULV), inwhich the active compound can be used even without additives.

The active compounds are normally employed in a purity of from 90% to100%, preferably 95% to 100% (according to NMR spectrum).

It was possible to show the action for controlling fish mycoses by meansof the following tests.

During investigations in small stretches of water for theecotoxicological estimation of fungicidal crop protection agents, fishwere also tested. Groups of 7 animals in each case of the speciesCyprinus carpio were kept under open air conditions in four containersfilled with 6.5 m³ of a natural beta-mesosaprobic water and naturalsediment. One container served as the control, the others were treatedwith various concentrations of the active compound I.2A-1 (correspondsto I.01 of the following table): 0; 1.3 μg/l; 6.7 μg/l and 33.3 μg/l.

The active compounds were used here as 50% by weight water-dispersiblegranules of the following composition:

50% by weight of active compound

10% by weight of carrier (ammonium sulfate)

1% by weight of Pluronic® PE 6800 (adduct of ethylene oxide andpolypropylene glycol, dispersant)

0.84% by weight of antifoam (33% strength aqueous emulsion ofpolydimethylsiloxane)

made up to 100% by weight with a 2:1 mixture of

sodium lignosulfonate and

the sodium salt of the formaldehyde condensate of naphthalenesulfonicacid.

The randomly distributed fish were put in on 04.25.94. On 05.03.94 afungicide treatment of the reservoirs was carried out. In the furthercourse of the test, 4 of 7 fish in the control reservoirs (no fungicidetreatment) became ill and died of fungal attack, no fish (but 2 beforetreatment) became ill and died at the lowest concentration and likewisenone of the fish became ill and died at the two higher concentrations.

That is to say whereas in the control a good half of the fish wereaffected by fungi and also died thereof, in the reservoirs treated withI.01 no fungal attack occurred. All fish remained healthy.

At the end of the test after several treatments, the growth in size ofthe fish and their general state of health was checked. During thecourse of this, no negative effects of the fungicide whatsoever werefound on the fish.

We claim:
 1. A method for controlling fish mycoses and single-cell ectoparasites of fish, which comprises applying to fish or their habitat an effective amount of compound suitable for inhibiting the mitochondrial respiratory chain at the stage of the b/c₁ of the formula IA or IB ##STR3## is used where . . . is a single or double bond and the index and the substituents have the following meanings:R' is --C[CO₂ CH₃ ]═CHOCH₃, --C[CO₂ CH₃ ]═NOCH₃, --C[CONHCH₃ ]═--NOCH₃, --C[CO₂ CH₃ ]═CHCH₃, --C[CO₂ CH₃ ]═CHCH₂ CH₃, --C[COCH₃ ]═NOCH₃, --C[COCH₂ CH₃ ]═NOCH₃, --N(OCH₃)--CO₂ CH₃, --N(CH₃)--CO₂ CH₃, --N(CH₂ CH₃)--CO₂ CH₃, R" is a C-organic radical,a C-organic radical which is bonded directly or via an oxy, mercapto, amino or alkylamino group, or together with a group X and the ring Q or T, to which they are bonded, are an unsubst. or subst. bicyclic, partially or completely unsaturated system which, in addition to carbon ring members, can contain heteroatoms from the group consisting of oxygen, sulfur and nitrogen, R^(x) is --OC[CO₂ CH₃ ]═CHOCH₃, --OC[CO₂ CH₃ ]═CHCH₃, --OC[CO₂ CH₃ ]═CHCH₂ CH₃, --SC[CO₂ CH₃ ]═CHOCH₃, --SC[CO₂ CH₃ ]═CHCH₃, --SC[CO₂ CH₃ ]═CHCH₂ CH₃, --N(CH₃)C[CO₂ CH₃ ]═CHOCH₃, --N(CH₃)C[CO₂ CH₃ ]═NOCH₃, --CH₂ C[CO₂ CH₃ ]═CHOCH₃, --CH₂ C[CO₂ CH₃ ]═NOCH₃, --CH₂ C[CONHCH₃ ]═NOCH₃, R^(y) is oxygen, sulfur, ═CH-- or ═N--, n is 0, 1, 2 or 3, where the radicals X can be different if n>1; X is cyano, nitro, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy, C₁ -C₄ -alkylthio or, in the case where n>1, a C₃ -C₅ -alkylene, C₃ -C₅ -alkenylene, oxy-C₂ -C₄ -alkylene, oxy-C₁ -C₃ -alkylanoxy, oxy-C₂ -C₄ -alkenylene, oxy-C₂ -C₄ -alkenylenoxy or butadienediyl group bonded to two adjacent C atoms of the phenyl ring, where these chains in turn can carry one to three of the following radicals: halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or C₁ -C₄ -alkylthio, Y is ═C-- or --N--, Q is phenyl, pyrrolyl, thienyl, furyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, thiadiazolyl, triazolyl, pyridinyl, 2-pyridonyl, pyrimidinyl or tridzinyl, T is phenyl, oxazolyl, thiazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyrimidinyl or triazinyl.
 2. A method for controlling fish mycoses and single-cell ectoparasites of fish, which comprises applying to fish or their habitat an effective amount of a compound suitable for inhibiting the mitochondrial respiratory chain at the stage of the b/c₁ of the formula IC ##STR4## is used where the index and the substituents have the following meanings: x is cyano, nitro, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy or C₁ -C₄ -alkylthio;n is 0, 1, 2 or 3, where the radicals x can be different if the value of n is greater than 1; R' is C[CO₂ CH₃ ]═CHOCH₃, C[CO₂ CH₃ ]═NOCH₃, C[CONHCH₃ ]═NOCH₃, C[COCH₂ CH₃ ]═NOCH₃ or N(OCH₃)--CO₂ CH₃ ; R is phenyl, pyrazolyl, pyridyl or pyrimidyl, where these groups can be partially or completely halogenated and/or can carry one to three of the following radicals: cyano, nitro, C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy and C₁ -C₆ -alkylthio and/or a CR¹ ═NOR² group or a phenyl ring which in turn can be partially or completely halogenated and/or can carry one to three of the following radicals: cyano, nitro, C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy and C₁ -C₆ -alkylthio;N═CR.sup.α R.sup.β or N═CR.sup.γ CR.sup.δ ═NOR.sup.ε ; R¹, R², R.sup.α, R.sup.γ and R.sup.ε are C₁ -C₄ -alkyl, R.sup.β is phenyl, pyridyl or pyrimidyl, where these groups can be partially or completely halogenated and/or can carry one to three of the following radicals: cyano, nitro, C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy and C₁ -C₆ -alkylthio; R.sup.δ is C₁ -C₄ -alkyl or phenyl, which can be partially or completely halogenated and/or can carry one to three of the following radicals: cyano, nitro, C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkoxy and C₁ -C₆ -alkylthio and/or a CR¹ ═NOR² group. 